The Art (and Science) of Breaking the Rules

you-are-told-1314479-1280x960It’s better to ask forgiveness than permission. How often have you heard this quoted, often with a laugh, to justify when someone just wants to do whatever they want to do? Does it mean that you should break the rules, or is it just an excuse someone uses when they don’t like the rules? As all project managers know, rules, policies, and procedures exist for good reason. They protect us, they help us coordinate, and they can save us time and effort by providing repeatable processes to follow. Companies create processes to help keep things organized and focused on the bottom line. The list of good reasons is long. We are all familiar with them. We even invoke them when we create the rules ourselves. The problem comes in when the rules are followed without thought or consideration. A poor manager follows the rules blindly regardless of the outcome. A true leader understands when to act outside the rules.

I have mentored many project managers over the years. One of the most common challenges comes when the project manager knows that the existing process will not produce the best outcome for the project, but none the less adheres strongly to the process. Often it’s because he fears that not doing so will harm his career or position in the organization, bringing disciplinary action of lack of promotion. He dismisses any negative outcome for the project as “not his fault”, insisting that it will be accepted as an appropriate result. There are definitely times when this is true. However, to really become a leader, it is critical to develop the ability to know when it is appropriate to break the rules, and to understand the appropriate strategy for doing so. The world is not a black and white, yes or no, binary options kind of place – processes and rules cannot possibly account for every possible situation. In order to succeed, we must learn how to work the uncertainties, push the boundaries, and identify when the rules need to be changed, or even broken, to reach the desired outcome.

Know the reason and intent of the rule. Before you can effectively diverge from an existing policy, you must understand what the rule is intended to promote. It is only by understanding this can you identify where your alternative course of action diverts from the rule and what the impact of your decision may be. This way you can look for opportunities to limit the impact of the action, or promote changes to the rule to address the new situation. For example, a standard process may be too expensive for a small project – you can propose a more limited approach that is better aligned to project resources.

Understand organizational priorities. By researching the big picture and what is most important to your company and the project sponsors, it demonstrates your executive thinking, and that you can show that while you will not be following a particular policy, you have made this decision in the best interest of the organization and the project, and can defend your decision in such a way that it can be supported by your sponsors and managers.

Document the reason for your decision. Define a clear justification for the action you want to take and be comfortable defending it. It will be your understanding of the intent of the rule, your consideration for the organization, and the clear reasoning for why this is the best course of action that will support your actions. Using a decision matrix approach, show the top options, what the expected outcome would be if the rule would be followed, and the expected outcome of the preferred response.

Make sure your entire team is on board, including stakeholders. Some team members won’t be comfortable breaking the rules, but if they trust you as a leader, and you have a track record of protecting and supporting your team, they will accept that this action is part of your responsibility as the project manager, and that “You’ve got this”.  Ideally, if you can, also let your stakeholders know ahead of time what you intend to do, and share your analysis with them ahead of time.

Ideally, you can present your decision to management, stakeholders, and team members prior to taking action. But even if you need to make a unilateral decision, you must conduct this analysis to be sure that your decision is one you can support and defend after the fact as well. Not only will this protect you, but will also demonstrate your leadership skills. You will have shown the ability to make the hard decisions in a professional, knowledgeable way – a critical skill for successfully navigating large, complex projects. You will also be providing valuable input to improve existing procedures. Make breaking the rules into the art, and the science, of good decision making.

Procrastinate Your Way To Success


I procrastinated writing this post. I got another cup of coffee. I talked to the dog. I checked Facebook. But, as you can see, I got it done.  But once I got started, I really got into it. This is by far the longest post I’ve written, and one of the most enjoyable to write. I hope you enjoy reading it.

I have been a procrastinator all my life. I’ve been chastised for procrastination my whole life by teachers, parents, and even peers. Yet I think I did pretty well, all things considered. I made good grades, completed college degrees, built a successful career, and all in all I have a pretty good life. However, I still beat myself up over procrastination. If I just didn’t procrastinate, I would be able to get so much more done, be more successful, and be happier. Do all those things that I say I want to do. I tried all kinds of methods. Scheduling time in the calendar, using various to do list and planning apps, and more. Being a project manager for so many years, you would think that all my planning skills would resolve the issue. But therein lies the problem. We try to schedule ourselves according to how we think we should work (or worse, how someone else thinks we should work). I’ve come to the conclusion that while procrastination can be a problem, it can also be a valuable tool. Sometimes procrastination is trying to tell you something.

Procrastination can tell you a lot about how you are working – how you feel about your work, how you work best under different circumstances, and can provide clues to how best to organize your life. When you think you are procrastinating, start by digging deep and think on why you are procrastinating. Then consider acting on the why first, and letting it inform how you complete the task. I’ve identified a few sources of procrastination to demonstrate this approach.

Procrastination tied to perfectionism. For example, I was always taught in school that when you get an assignment, you should start working on it right away, and work diligently until it’s due. This way you can make sure it is complete and polished and get a good grade. Now as an adult, I give a lot of educational presentations for project management groups. These are typically 45 minutes of content. I’ve done a lot of them, so I have a solid slide structure that supports my internal timing. I know how to put a professional training presentation together. Of course, I always do them at the last minute, and I still beat myself up over it. Could they be better if I worked on them longer? Rehearsed more? Spent a few hours finding better graphics, or funnier stories? One day I realized – I’m not really procrastinating – I’m subconsciously improving my efficiency. My presentations are very professional and well received. The amount of improvement I might achieve are not worth the many more hours I would spend. Let go of the perfection monster. Being comfortable with good enough actually frees you to do more with your time. I gave up thinking I should start earlier, and accepted that this is my method and it works just fine.

Procrastination tied to aversion. Sometimes we have to do things we don’t like to do, don’t want to do, or are afraid to do. Procrastination in this case seems to me like a very rational response. I put stuff in to-do lists, plans, calendars, and yet I still procrastinate. Why doesn’t it work? Because constantly nagging yourself to do what you don’t want to do hits us right in our lizard brains and makes us want to do the tasks even less! So accept that procrastination is telling you something, and rather than run at it directly, try using a distraction strategy. A distraction strategy allows you to re-define the task in a way that associates it with a positive reward in some way. For example, I hate to vacuum. My husband hates to vacuum. We really, really hate to vacuum. So I don’t. Even with three dogs, I’d rather watch the dust bunnies float across the floor than vacuum. However, my husband and I love having guests over for dinner. We are known for throwing impromptu barbeques for 20 people. And guess what? The house gets vacuumed – usually an hour before people are due to arrive. I don’t hate it any less, but I’m OK with it, since it means soon all my friends are showing up. We noticed this pattern a while back, and now it’s part of our methodology. “Let’s have some people over – the house needs cleaning!” But what if it’s a task you are afraid of. Are you afraid you can’t do it, or are you afraid it won’t be perfect. If you fear not being perfect – go back to the previous paragraph. Let it go. But if you are afraid you can’t do it, try breaking it down into small tasks and creating a game or contest with yourself (or others) to distract you. This also works for other tasks you hate, like exercising, writing reports, etc. Create a progress chart. (You can also use a calendar for this). Define a small subtask each day, and then give yourself a sticker when you complete that day. It’s funny how you might hate that 30 minutes on the treadmill, but you love seeing that unbroken string of stickers on the calendar. Pretty soon the task has changed from hitting the treadmill to not letting the streak lapse. This becomes even stronger when you display your progress streak publically. Now that can be scary – but start with your friends – let them help you.

Procrastination tied to desire. This one really hit me when I saw it for what it was. How much of my to do list, both professionally and personally, was tied to things I thought I should be doing to be successful, things other people I admired were doing, and things that I thought I should be doing if I wanted to be the best, most successful, most admired person I could be. OK, maybe I’m overstating that last bit, but it is true that we surround ourselves with a lot of “shoulds” in our lives. Tina Fey, in her book Bossypants, wrote “When people say, “You really, really must” do something, it means you don’t really have to. No one ever says, “You really, really must deliver the baby during labor.” When it’s true, it doesn’t need to be said.” So often we absorb ideas and experiences of others into our minds and turn them into jobs for ourselves. I’m an idea-person. I constantly think of things I could maybe do. I used to put them on a to-do list. Now I have a note pinned to the top of my-to do list. “Not all ideas are tasks to be completed”. I recently read Marie Kondo’s book, and I liked the underlying concept of examining our stuff for how it serves us, and jettisoning the things we are keeping around for reasons unrelated to having a joyful life (I paraphrased a lot there). When I tried it, I found I was storing an amazing amount of gear, supplies, and just general stuff because “someday I would like to …”, ending that sentence with some craft, project, or product that I could imagine myself maybe doing someday, but I kept putting it off. For years, and years. The lightning bolt hit – I was procrastinating because I was never really going to do that. I love to tinker with crafts. But when I got rid of about 80% of my craft stuff that sat untouched for years, I found that I’ve worked more with the items I kept than I ever had before. I just had to get rid of all the other stuff, the “false tasks”, that were gumming up the works. This works for digital hoarding as well. “KonMari” all the articles you haven’t read, courses you haven’t taken, books you haven’t opened, blog reader queues overflowing, and the other “shoulds” that are clogging up your life so the really important stuff is front and center, without distraction. Procrastination can teach us that less truly is more. Let it go.

Getting The Most Important Things Done

Hdiary-page-1240501-1919x1521ow is it that I can get to the end of the day, exhausted from hours of “crazy-busy”, and still feel like I’ve gotten nothing done? Days filled with meetings, phone calls, responding to data calls, and generally living in reactive mode can leave you with little time to get your own tasks done. And then, when you find a few minutes to work, you pluck some “low hanging fruit” to complete, just to get something – anything – off your list.

A quick internet search will reveal more calendar applications, to do list managers, time management systems, and a myriad of tools and techniques for “getting things done.”  Like most professionals, I use some of these tools to try to manage my work. I have extensive, well organized to do lists, detailed project plans, and still I struggle. So much of my consulting work is to support other leaders in meeting their goals and successfully completing their projects that it often means that my time is not necessarily always mine to manage. And when I do get work done, it is often done in small chunks between meetings – which means while I am clicking things off the to-do list, the completed tasks tend not to be the most critical tasks. I end up working late, after everyone else has left, to get the bigger tasks done. So instead of putting the rocks, then the pebbles, then the sand into the jar, I fill the jar with sand, then try to buy new jars for the rocks. And to strain the metaphor even further, there is no room left for any more jars!

I finally came up with a simple strategy that has helped me immensely. The key here is simple. This method does NOT scale. It won’t manage a full to do list, and it is not a new system. It doesn’t even have a catchy name. Think of it as professional “me time.”

What is the most important single thing I want to get done today? Tomorrow? Next week? Choose one task – Ideally one that can be finished in about 45 minutes focused time. If the most important task would take longer, then define a sub-task that can be completed in the timeframe, and that becomes your day’s goal. Remember, choose a rock, or a part of a rock – not a pebble or bit of sand. Identify one for tomorrow, then start thinking ahead for a few similar tasks.

Schedule an appointment for yourself. Block one hour on your calendar. Create a meeting entry, showing busy, or even “out of the office”. Make it a private meeting. I find that the first hour of the day or the first hour after lunch to be the best times for me, but try to schedule it at your most productive times of the day.

Prepare the details. Attach all the information you need to complete the task into the calendar entry. Don’t just be generic when you schedule the time – be specific about the precise outcome you need. Spend a couple of minutes preparing the workspace. Attach or link to any needed source material. Avoid any potential distractions by being prepared for the task as you would prepare for an external meeting. Be ready to jump right in.

Schedule these tasks out one, two, or even three weeks out if you can – this blocks your calendar before it fills up with meetings. As you identify each day’s “focus task”, list out a handful – just a handful – of critical tasks that you must get done in the next week or two. Scheduling ahead helps with limiting challenges to your reserved time, but also studies show that people are more likely to schedule unpleasant or difficult tasks in the future, but pick easier or more pleasant tasks for the near term. For cyclical tasks, I schedule recurring appointments to plan for them. I also set calendar reminders as well.

Be realistic about what you can do. The key to making this work is to keep the appointments with yourself. This means to use the technique sparingly – no more than one task per day, a couple days a week at most. If you try to do too much, you will start missing appointments, which defeats the purpose. Too many blocked off hours, and people will start catching on, and try to schedule you anyway. Lastly, make sure that you have defined the work to be able to easily complete it in an hour – 45 minutes focused work with transition in and out. After all, this is about getting things done. Add this approach to your time management arsenal to scale the big rocks in your day.



Practice Positive Expression to Inspire Your Team

photo-1415243931302-9eb5b22247f2Have you ever had a boss for whom the only communication was yelling? Or the manager who never seemed to be satisfied, no matter what you did? Or the leader who thought that the only way to motivate was criticism and competition? Did this approach inspire you to do your best work, or just enough not to get yelled at or fired?

As a leader, have you ever expressed to your team that you thought the project would fail? That your product was a lemon? That the organization wasn’t giving you the resources the project needs to succeed. How many times have you commiserated with your team that everything was going wrong and you were sick of it? I’ll fess up – I’ve done it. And you know what, it was a big mistake and I’ve regretted it ever since. Your team is not there to be your mother, your spouse, your best friend, or your dog. It’s fine to complain to them. In fact, I highly encourage complaining at will to your dog. It’s highly therapeutic. (In my experience, cats have no patience for these conversations and walk away – they have better things to do.) Your job as a project manager and as a leader is to be supportive of your team. Yes, you must be honest about problems, and face up to issues as they occur, but you must also be a positive voice of encouragement, no matter how you may feel.

I don’t generally consider myself a naturally optimistic person. I’m a pessimist, though I usually say I’m a realist. I tell people being a realist means that I believe in identifying all possible outcomes. But if I’m honest, I really mean that I believe that if something can go wrong, it probably will. While this has probably contributed to my successful project management practice over the years, it doesn’t always make me feel like a success on a day to day basis.  I shared this with a colleague this once, and she was genuinely surprised. “But you always seem so positive! Everyone looks to you for encouragement”. I laughed when she said this, and probably said something self-deprecating. But could both of these things be true? Can you be imagining the walls collapsing around you while keeping your team marching toward success?

I have learned that while it is important to examine what might go wrong, if you don’t believe something will succeed, you shouldn’t be doing it. So how to you turn negative thoughts into positive expressions? By policing your language. Don’t complain about the organization or your customers. Don’t deprecate other leaders or teams. Focus on what you can control. Instead of saying “This will never work”, say, “We have a solid plan. If we follow the plan, we will succeed.” Then make sure you are following the plan. Approach changes not as acts of desperation, but as opportunities that come from what you’ve discovered on the project.

You can also practice compassion. Instead of saying “Judy is so pathetic. She’s always late with her statuses.” Consider that maybe Judy is dealing with a challenge. Go to Judy and say “I know it’s sometimes hard to get the status reports done with everything else going on. Is there something we can do to help?”

I’m not saying you must be a Pollyanna. Bad things will happen, and hard truths must be told. A leader must be the point where reality is addressed. But avoid blame, complaints, and un-productive negative expression. This type of talk drains the energy from your team. Negative predictions have a way of coming true. Instead, look for positive ways to address the same information. Use language that, while acknowledging the problem, focuses on a solution. This works not just for external communication, but it also works for your inner monologue as well.  Practicing positive expression in my thoughts about myself has made a huge difference, and allowed be to break through some of my own negative thinking. Policing your language can be a form of “fake it ‘til you make it” – finding positive way to express yourself to your team may just help you find a more positive mindset, and even help you find solutions. No one wants to be part of something that will fail – don’t undermine your leadership by being negative.

And go ahead and talk to the cat – just bring some treats along.

Distributed Team Not Communicating? Build a Virtual Team Room!


Managing communication is critical to successful projects, but when our project team is distributed across locations, time zones, countries, or even continents, good communication doesn’t come naturally. One important challenge is maintaining stable consistent communication channels across the team. When the team is not co-located, we can’t rely on proximity and incidental communication to distribute information. We have many electronic tools in available to us, from email, conference calling, web collaboration tools, cloud file sharing, the list goes on. We have all the tools we need – so why is important information still being lost? Why do we still struggle to collect, analyze, and disseminate information to the right people at the right time? Why do we spend so much time answering email and sitting in endless conference calls? Because we have the tools, but not the plan for what, when, and why to use them. So how do you select, deploy and use the right tools to serve the project needs?

Consider building a virtual team room. What is a virtual team room? Think of it as an electronic representation of a project team room. Project team rooms provide a place for team members to come to get information, hold formal meetings or information discussions, work together without external distractions. They are familiar places to many of us. The goal of a virtual team room is to build an integrated network of communication tools that are accessible equally by all team members, allow for timely communications among all appropriate team members, and provide accessibility to project information. The electronic tools are the resources – it’s up to the project manager to decide which tools will be used, and how they will be used, and to train and reinforce the use among team members. The virtual team room is the construct that informs the plan for and use of those resources.

Imagine a project team room. For this exercise, picture a good sized room with a large conference table at one end. There is a white board on the wall next to the table, and a projector on the table, projecting onto the far wall. Along the two other walls are work cubicles with work tables for individuals and small groups to work. And at the other end is a wall sized bulletin board displaying the project plan, schedule, recent successes, upcoming deliverables, project announcements, and anything anyone wanted to post. Lastly, there are several file cabinets containing previous deliverables, reference material, supplies, and work products. For a co-located team, everything they need to complete the project is in or accessible from this room. Now what if half of the team is in another state?

Replace all the physical resources with electronic ones. Replicate the room virtually, and use this visual construct to organize communications. Instead of the large conference table at one end, you have conference calling. Sounds obvious, but set a policy that before sending that one-to-one email, consider whether it’s a conversation that others may want to hear, and could the issue be resolved more quickly with a short meeting? Would you have called an impromptu meeting at the table? Use the conference line instead. For the white board and the projector, use on line collaboration tools. Bulletin board, file cabinet – we have tools like SharePoint that can serve these functions as well.

But that is just the first step. The second step is to develop a set of guidelines for using the tools, with the goal of insuring that all team members have full access to information, full participation in the project, and maximizing the productive time of the team. Would you have all your team members sitting at the table for hours every week listening to you talk? Instead, post the information on the “bulletin board”. Does the engineering team need to review and discuss the latest test results? A collaboration tool where the results are visible to everyone, and each team member can participate in the discussion and they can work together to craft the response. A discussion page can allow for detailed conversations even if team members are not in the same time zone. Each team member should come to the virtual team room to work, just as they would come to a physical team room.

And just like you would monitor your team’s behavior in the room, as the project leader you must make sure to define roles and responsibilities, manage processes and controls, and be observant of the amount of participation of all team members, particularly if members are in distributed time zones. You must also monitor the use of the tools – not just whether the team members are using the tools as planned, but are the tools serving the project team members? On red flag is if team members are using “unauthorized” tools or using tools in unplanned ways. Before taking corrective action, find out why the team member has strayed from the plan. You may find that it is the plan needing corrective action, not the team member. Work with your project team to make adjustments to meet their needs.

The number of collaboration tools is increasing every day. Many of them are now web-based, inexpensive or even free. That’s great news, but it also means that using too many tools without a plan can increase confusion and make communication worse. I can buy a power tool, and even learn how to operate it, but if I don’t know the proper use of it, and when to use it, or have reason to use it, how does it serve me? It’s just another toy sitting in my garage. The virtual team room is a visual approach to the what, when, and why of project communications.

What To Do If You Don’t Know Everything


I remember very clearly the first time I was put in charge of an entire project – the planning, the staff, the customer, the contract, everything. That first day was certainly exciting, and while I was pretty sure I could do it, I was very, very wrong about one thing. That one mistake, had I not corrected it, could have contributed to failure on not only that project, but any future project I took on. What was the mistake? I thought it was my job to have all the answers.

Sounds silly to write that now, but it’s the truth. I was really worried that if I didn’t have an answer to someone’s question, they would think I didn’t know what I was doing. They would think I was in over my head, unqualified, a loser, etc. Pick your favorite criticism. That was a long time ago, and fortunately for me I had some wonderful mentors and colleagues, and they helped me quickly learn one of the most important secrets to success. Here it is: It’s not whether you know the answer, it’s how you handle the question.

So what does that mean? In summary (to paraphrase the serenity prayer) it means to know well what it’s important for you to know, understand how to manage what you don’t know, and be sure to know the difference. So how to you do this? Begin by being well versed in your professional skills. For me, this meant being strong in project management fundamentals. For example, my schedules and budgets were strong, with good bases of estimate behind them. I also had a good grasp of the customer, as I had some experience with them before. But what about all the stuff I didn’t know, like the technology and the area of business we were transforming? I came to realize that to be successful, it was my role to make decisions, secure resources, and support my team in completing their tasks. For me, “knowing the difference” is remembering to focus on the results and outcomes, and resist the urge to dig into the analysis or the technological solutions.

Surround yourself with people more knowledgeable than you. Whenever I am putting together a project, I try to find the smartest, most capable, and most knowledgeable people I can find. It is important to have a good mix of skillsets, experience, career level, and style. By assembling a really strong team, you have the beginnings of meaningful debates, good advice, and the ability to reach an exponentially larger pool of information and capabilities. As a project manager, you have access to a wide range of advice and options. It is true that sometimes having a team of high-performers can result in conflicts and competition, a good project manager maintains the standards of communication, makes sure everyone stays in their “swim-lane”, and that each team member is fully engaged in the appropriate project tasks.

Learn how to ask questions strategically. One of the biggest leadership competencies needed when managing “experts” is understanding how to talk with them. You certainly can’t learn their profession or expertise in order to understand them. What can you do? Rather than asking a single question, or asking “what should we do”, focus on having a progression of questions focused on decision making. Don’t focus on the how – that can get you down a rabbit hole of details that aren’t important to you as the project manager, and will often be too esoteric anyway. Instead, focus on understanding approaches, alternatives, risks and rewards, and outcomes. For example, assemble the work team, and have the team lead mostly speak for the team. Some questions you could start with include

  • How did you approach the problem?
  • What alternatives did you consider?
  • What are the top three options? Which option do you recommend? Why?
  • What options did you reject? Why?
  • Describe the biggest risk of each option.

These are somewhat generic, but hopefully this will be a starting point. Developing the skill of asking good questions will serve you well in any endeavor.

Develop a professional advisory committee. This is one of the most useful resources that every professional should have. In your career, you will build a network of colleagues that you like, respect, and trust. While it’s nice to meet for coffee or a cocktail from time to time, a better way to build your professional relationships is to reach out for advice and counsel, and provide such assistance in return. Use these friends as your sounding boards, as a way to verify assumptions or gut check your ideas. You are not asking them to do your work or make your decisions, but as another voice, another set of eyes, another viewpoint to make sure you aren’t missing something important. And if they’ve faced a similar situation, their advice will provide further information to support your decision making.

How you find out is more important than what you know. No human can know everything. Not only that, but you don’t know what you don’t know until you need to know it. There comes a point where you can learn to rely not on what you know, but your skills in learning and “finding out”. The biggest mistake I made on that first project was that because I thought I had to know everything, I said what I thought was probably true. Bad idea – I messed up a few times because of it. But then I learned that it was perfectly acceptable to say “I don’t know, but I know where to get the information you need. May I get back to you in the morning with the answer?” It is your professional responsibility to tell the truth. When I interview people for positions, I don’t usually ask much about what they know. Instead, I focus on how then approach problems, how they learn new information, and what they do when they make an error. This is the most important skillset for success. Being able to manage unknowns is a critical leadership skill, and project managers, in particular, must be well versed in it. Projects, by their nature, involve the new and untried in some fashion. That is why project management is so exciting. For leaders, it’s where true value-add is found. So whether you are a project manager, the leader of an organization, a domain expert, or all three, it’s not what you know, it’s how you manage the unknowns that matters most.